Almost every entrepreneur has had to decide whether to take the leap now or wait– perhaps they wanted to acquire more capital, experience or connections. Given how common this predicament is, we asked some successful business owners to reflect back on whether they wish they had started sooner or waited for a better time.

Mandy Welch

I wish I would’ve started my business sooner in life. I was 44 years old when I opened Best Friend Forever K9. I’ve always wanted to work with animals, but didn’t really know that you could make it a real job! I also didn’t have the confidence earlier in my life to do something like this. When I opened Best Friend Forever K9, I had been working for another company for about 1 year. I realized that I could do this on my own. My husband is so supportive and ensured me that I could do it. And if it’s something that I wanted to do, then just go for it! And here we are! I started training, with 1 dog in my garage. I later added boarding and 2 training dogs at the same time, with a max of 9 dogs at a time. Read more>>

Kendra Chanae

Absolutely! I wish I would have started a lot sooner than later. I started my singing career back in 2023. At the moment I work in the healthcare industry, servicing patients in need. If I would have started sooner, there is no telling who many great opportunities would have been opened for me at a more younger age. But I am thankful for the opportunities that I have right now. I couldn’t be more thankful and grateful for it all. Read more>>

Jaclynn Buchanan

I wouldn’t change a thing or go back in time! I believe in divine timing, trusting that everything unfolds exactly as it should. I’m truly grateful for starting my agency at this point in my life. After nearly 15 years in the industry, I’ve gained a depth of knowledge that I couldn’t have acquired any earlier. I’ve had the opportunity to work with a wide range of personalities, each one shaping me into the business owner I am today. These experiences have given me valuable insights into what I love and what I want to avoid, helping me make the best decisions for my business and clients. My background in fashion, social media, and talent management has significantly influenced my vision as an agency owner, allowing me to take a fresh approach and do things differently. Read more>>

Tye Erskin

I wish I started my career earlier, however I often think… the me back then, could he have handled this dream. I started comedy in 2019 and it was an adjustment to working for myself. Promoting myself and booking my own gigs. As I continue along this journey I gained more confidence in myself and my work that promoting myself now is no issue. Although I wish I started earlier starting when I did made all the sense in the world Read more>>

Rachel Shepherd

If you would have asked me three years ago or even six months ago if I would go back in time to start Loft Six Collective sooner, I would have said ‘yes’ in a heartbeat. Recently, I think that’s something I am learning to let go of as I am settling into my groove. I am a big believer that everything happens for a reason and that your life path will change based on the choices you make. Perhaps I say I wish I could go back, then I wouldn’t be exactly the person I am today doing the things that I am doing. If I started then, I don’t think I would have had tough enough skin to be honest. I wasn’t ready and that’s what is helping me accept that it’s okay to let those “what if” thoughts go. I started when it felt right and I haven’t looked back since. Sure, I would have more experience with this, maybe my skills would be more sharp in a certain area, but I have so much time in my future to continue my pursuit. Read more>>

Johnny Rodriguez

If I could go back in time, I would absolutely have started my consulting business sooner. Consulting is something that has always come naturally to me, but in the early years, I often found myself offering advice and strategic insights for free. I’ve always had a strong ability to assess businesses across various industries and provide actionable suggestions to drive revenue growth and enhance brand awareness. Read more>>

Sarah Dowds

I definitely do wish I had started my business sooner, but truthfully, I really believe that timing happens how it should & I have zero regrets. I think if I had started any sooner, I would have hit a lot of bumps in the road & possibly quit too soon. I never had intentions to work for myself, but the way situations & opportunities aligned, at the time that I decided to do this, I had zero doubts that it was the right move. I had never felt that strong of a push to start my own business previously, so again I think if I had started earlier, it would have felt & been a little premature. Read more>>

Federico Peri

Looking back, I wouldn’t change the timing of when I started my business. I launched it in the late 2010s while I was working for an Italian architectural firm, and it felt like the perfect moment to embark on a new adventure. The decision was driven by a deep passion for design and, perhaps more importantly, a strong desire for personal change. Read more>>

Jamme Alexander

I wish I would have started my entrepreneurial journey earlier. Being a natural born leader it is very hard for me to stay in one place for too long! In 2021 I decided to move from Nebraska to Arizona to grow my businesses. I was a stay at home mother at the time and had just became certified as a software developer. I started a business in tech but while building that vision I needed income to invest into it! I had done several events with my families catering company and have over 20 years of experience in the service, sales and hospitality industry. When we arrived I instantly went into “Grind mode” as I do. I ran across someone looking for a bartender on facebook for a private (in-home) event and he asked me if I could do it! Read more>>

Marco Carreira

If I could go back in time, I’d say starting my business sooner would have been the way to go. I launched my personal finance coaching business in 2019 while working full-time as a software engineer. At that point, I was comfortable in my career, but I wanted to do more with my passion for helping others with their finances. Starting earlier would have meant gaining more experience and building the discipline needed for running a business, because it’s a long process, and every day is an opportunity to learn and grow. The earlier you start, the more you can build on that foundation. Read more>>

Pollethe Ramirez

Looking back, I often wish I had started my marketing company much sooner. For years, I was comfortable in my routine, enjoying the stability of a job I liked, yet constantly thinking about the entrepreneurial path that I never quite had the courage to pursue. The thought lingered, but I kept holding back, too afraid to take the leap. It wasn’t until I was laid off that the decision was made for me. After landing another job, it quickly became clear that something was missing. The spark just wasn’t there. That’s when I realized it was time to take a bet on myself, and I haven’t looked back since. Read more>>

Brandon West

I believe I started my business venture at the right time for me, but I wish I had leveled up sooner. Before I explain that I’ll share how I got started. I was in college and completing an internship during the summer. Me and one of my closest friends had always joked about having our own celebrity blog/platform, and literally just one day I got home from my internship, I texted my friend and said, “We’re doing it. Let’s think of a name… I’ll start on the website right now.” I designed the website and we came up with our brand in about three days, got a couple blog posts done, and then launched within about two weeks. Read more>>

Ebony Williams

I wish I would have started working with people sooner. I decided to start my business while I was getting my Masters degree, but I had to stop because between school, my parents being sick and going through a divorce it was too much. I couldn’t focus on anything because I was in a full flare due to my autoimmune disease. I officially started working with clients in 2019 almost 10 years after getting my degree in Exercise Physiology. As much as I would have liked to have started my business sooner, I wouldn’t be the trainer and coach that I am today. Our lived experiences contribute to our ability to serve clients and all of those things created a perfect foundation to provide better care. Read more>>

Allison Prince

I believe everything happens for a reason, so I do not wish I had started my photography business any sooner or later than I did. I had been a nurse for a little over 3 years and had been doing photography as a hobby for the same amount of time when I first opened my photography business in 2022. At the time, it was my side hustle. I never imagined that photography would later become my full time career. To begin, I will explain why I am glad I did not start my business sooner and then explain why I am glad I did not start it later. Read more>>

Stephanie Wells

I would definitely have started my business sooner if I knew what it took at the time. It has been so fulfilling to create something so meaningful to me and my clients, and I only wish I could’ve had more of this for a longer period of time. I was working for a waxing corporate chain for almost four years before venturing off on my own. Before that, I worked in a salon as a receptionist and esthetician doing luxury facials for Aveda. I very quickly realized that I work best on my own, and I like the idea of being able to do my career in the way that works best for me. Read more>>

Lo Werth

If I could go back in time, I wouldn’t change a thing about when I started my business. In January 2023, after feeling burned out from my 9-5 career in behavioral health—helping others through recovery and severe mental illness—I took a leap of faith and started something new. Had I started earlier, I wouldn’t have gained the vital experience in organization, people skills, and patience that I rely on today. I also wouldn’t have built the incredible network of amazing people who support me now. Things fell into place when I was truly ready to go full force. Looking back, I realize starting sooner might have meant missing out on being fully prepared. I’m grateful for the timing—it was the perfect moment to take that next step! Read more>>

Shenitra Landry

If I could go back in time, I would have definitely started my baking business earlier in life. I started baking as a business about 8 years ago. Prior to that I would bake here and there and sell cakes and cupcakes to friends/co-workers. Back then it was more so a hobby vs a business and what I would charge would basically cover supplies only. I do feel like if I had the business mentality back then, I would be further along than I am now. However I also feel like everything happens in due time. Read more>>

Jackie Thomas

I officially launched my business and turned my website on 4 days after my 40th birthday. In hindsight, I wish I had started it months, or even years earlier! Though I had been working on it for quite a while, I never felt completely ready to be “official” and kept putting it off for various reasons. Life-wise, I was in a good place to start when I did and while it would have been harder to start earlier, I still wish I would have. Starting a business is like preparing for a baby- you can research, read all the books and prepare nonstop, but when it comes down to it, you still feel clueless some days. Read more>>